How to plan big group trips, from family reunions to friend gatherings

In 2023, my husband, Bill, and I visited the small, out-of-the-way town on the Greek Peloponnese peninsula where my great-grandfather was born. My cousin Alex inspired me, having made his way the year before — the first from our American family. I met the kindly relatives he had found there, and, like him, reveled in the beautiful mountain setting.

Afterward, I told my uncles (my late father was one of five sons) about my trip and offered to assist anyone who wanted to take a similar one. “Let’s go!” they said. “How about next year?”

Word spread to the rest of the family, and suddenly, I found myself planning an overseas vacation for a whopping 31 relatives, some of whom I hadn’t seen in years.

While I was initially a bit overwhelmed at the size of the group, I came to realize it gave us the advantage of scale. I contacted a few tour companies in Greece, ranging from full-service to transportation-only, and settled on a middle ground: a company called, fittingly enough, Private Tours Greece. They arranged transportation — we had enough people to fill a full-size tour bus — lodging, and entry to historical sites. I planned the five-day itinerary.

We made the trip last September, and we had the time of our lives. Not just because the adventure was memorable, but because it gave us precious time with people we care about.

One of my favorite things is exploring the world with groups of people I like. As a travel writer, I’ve met many other successful groups over the years, too. Here are a few tips, based on what I’ve learned, for how to organize a group trip, whether it be a big family reunion or a bunch of friends reconnecting over a shared love of exploring new places.

First, and perhaps most important: Go with people who get along. My family group ranged in age from 18 to nearly 80, and we all have our own personalities and viewpoints. But we enjoy one another’s company. I credit my grandparents, who brought us together often for fun times and set an example of nonjudgmental love. A group doesn’t have to be family. One of my favorite things is travel with easygoing friends, who are family in their own way.

Someone has to be in charge. I won’t lie: I felt some trepidation when I climbed onto that bus and the driver handed me a tote bag labeled “tour leader.” But hotel managers, attraction guides and the bus driver needed answers from someone. While I don’t normally like being responsible for other people, my zeal for research and my experience with travel in general, and in Greece specifically, made me the logical fit in this instance. Meanwhile, I’ve found that most people (including me) are generally happy to go along if someone else does the planning.

That said, the lead person doesn’t have to be the same for the whole duration. On a Vancouver Island hiking tour a few years ago, I met a group of women who were high school friends, grew apart, then reconnected years later. During their shared vacations, each woman gets what they call a “birthday.” She decides and plans what they will do on that day, and everyone else goes along for the ride. However you structure it, it’s good to know where the buck stops at any given time.

But delegate. In one of our early planning meetings, I told my uncles that I was good at planning, but not so much at wrangling people. “I’m good at that,” my Uncle Nolan said. I took care of the research and putting the itinerary together. He ascertained who was committed to going, kept everyone notified of developments and made sure everyone paid their share. 

Meanwhile, my cousin Alex, the first to venture to the homeland and already beloved by the relatives there, took on the role of “Greece family liaison.” My cousin Jodie was what I called the “cruise ship social director.” She helped us check into and out of hotels and passed along important information as it arose during the trip. Delegating some of the work took a mental load off me and gave more people a chance to be involved.

Make plans, but be flexible. Our itinerary had us riding a historic train early one afternoon and then visiting a museum at the end of the ride. But I learned the museum would be closed by the time we got there. It was important that we go to the museum, where we could learn more about the local people, so we went back another day. If we had booked ourselves up too solidly, that wouldn’t have worked. Leave some room for changes on the fly.

Schedule together time and alone time. If you’ve been stuck with an “I want us to do everything together, all the time” person, you know how wearing that can be. But if everyone scatters to do their own thing, you lose out on valuable shared experiences. On our Greece trip, scheduling one or two main group activities per day worked great. For most lunches and dinners, we broke up into small groups. We left evenings open so folks could decompress and get to bed on their own schedules. We made the ancestral hometown a base so we knew what we were returning to each night and could settle in there.

Transportation can be a challenge — but also an opportunity. When we first started planning, we thought about renting cars. But with a group that big, hiring our own bus was surprisingly economical. And transportation — getting lost, being late, figuring out how long it will take to get from one place to another — is often one of travel’s most stressful aspects. We ended up loving being together on the bus, reminiscing about old times and making a whole new set of friendly jokes about one another. 

Our driver, the friendly and accommodating Panos, was there to look after our stuff while we visited sites. And he spoke Greek and knew his way around, which helped immeasurably. Panos, whom we nicknamed “Iceman” for his ability to keep a cool head while navigating twisty Greek roads, was thrilled at the chance to drive that big bus through hairpin turns up a mountainside so we could all visit a remote village (current population: about six) where my great-grandfather spent part of his life.

You don’t need to book a full-size bus. My friend Doug, a frequent planner of group trips, rented a smaller bus for a Portugal wine-tasting tour with about a dozen friends. Trains are an option in many places. The bottom line: Consolidate transportation and see if you can hire a professional to get you around. You might have more options than you think.

Be game. If you’re not the one doing the planning, cheerfully following the plan will contribute a lot to making a trip successful. One of the things that made our Greece trip so fun was that people went with the flow. Whatever was on the itinerary, they were up for it. As my cousin Micol said, “Always look for the adventure in everything you do!” 

On our first night in the small town, my family members headed out to restaurants, navigating language and cultural barriers. Not only did no one complain, they were soon posting selfies with local merchants on the shared family WhatsApp group. (Speaking of the WhatsApp group, I highly recommend setting up some form of group chat for the trip — if you’re traveling internationally, something that doesn’t require cellular service.)

Remember why you’re together. Our adventure heightened our sense of appreciation for those who came before us — the sacrifices they made and the work they did to build a life in the U.S. It also taught us more about the sometimes difficult lives of the family members left behind in Greece. It strengthened our feelings for one another and our far-flung relatives. 

While we saw lots of cool places and did fun things, ultimately, the trip was about people. In my experience, all the best ones are.